In today's commerce, merchants often utilize an array of different point-of-sale (POS) devices, including mobile POS devices. Merchants may use these mobile POS devices to engage in transactions with customers at different locations. For example, a barista may use a mobile POS device to charge a customer for a cappuccino. In another example, a food truck may use a mobile POS device to charge a customer for lunch. The mobile POS devices are configured to operate in either an online mode or an offline mode. While in the online mode, the mobile POS device transmits transaction information to and from third parties over the internet at the time of the transaction. In the online mode, the merchant using the POS device knows if a transaction is successful (i.e., if a card is approved) prior to the customer departing the store. Therefore, there is generally little risk in the merchant losing money while operating in the online mode. While in the offline mode, however, because a merchant does not know whether a payment instrument will be approved until well after the customer has left the merchant, the merchant may risk an unsuccessful transaction.